Timing
by AnnaTW
Summary: Nothing ever happens at the right time. Tony/Pepper
1. Chapter 1

**Stole this idea from 'The Ugly Truth' but I imagined how it would go between Tony and Pepper and just **_**couldn't**__**not**_** do it. Got a lot of love for them at the moment. (P.S. sorry this starts off slow.)**

It sounds like a simple love story at first, but it really isn't. People and feelings have complicated things for Pepper, _and_ Tony, _and_ Jake. And no one could figure out the best solution. So here's the back story.

Jake Henderson. A well-built, tanned, light haired man. He lived in Los Angeles his whole life with his parents and two sisters, he then eventually moved out at the age of twenty and has lived on his own since. He went to college and became a lawyer. He hadn't always wanted to be one, but he liked the sound of the course and one thing just led to another. So at the age of twenty five he started working for Grayson's lawyer firm. He was a popular man with his fellow male colleagues. Jake was 'one of the guys' and so could be quite crass at times. His sisters tried to keep him grounded and develop a more emotional side to him, but Jake liked being a man. He wasn't very committed as of yet, not because he didn't want a relationship, but because he'd only ever met the wrong type of woman.

But then he met Pepper.

They bumped in to each other in a quaint coffee shop on a Saturday afternoon. Pepper was reading one of her old favourite books in the sunshine and Jake was buying breakfast for the girl he managed to snatch from the club the night before. She had to go and do some volunteer work or something and so left Jake drinking his tall Frappuccino on his own. Then he spotted Pepper.

And it was pretty simple from then on. He went over, they talked, and they've been dating for three and a half months now.

Three and a half months of fun. Pepper had tried to have a relaxed approach towards their relationship because it seemed like Jake Henderson was a very laid back guy. And that was what made Jake so happy to be going out with Pepper. She was cool and interesting and gorgeous. And she didn't pressure him to be some amazing guy who he just wasn't. Despite the fact Pepper wanted Jake to step up and be a gentleman in the relationship, she was taking things one day at a time.

Especially because of Tony Stark.

Pepper loved him. She _really_ loved him. And she was fine to admit it, she just hadn't figured out what that love was yet.

When Pepper first started dating Jake she wanted Tony to know. Not to rub it in his face, but she didn't want the awkwardness of him finding out accidently. So after her and Jake's fourth date, Pepper decided to tell Tony. She gave him his day's events and once she ticked the last one off, she just came out with it. It was clear that Tony was surprised, and even hurt, although he tried to hide it. In the end Tony congratulated her and went back to his work.

They had been their usual jokey selves' mere hours after she had told Tony and so she thought she was in the clear. And she was right; of course she was in the clear of Tony. But not necessarily of her _own_ feelings. They had played around the subject too much and having not even _kissed_ Tony before toyed with her heart. She didn't know who or what to trust.

She knew Jake was a great guy, attractive, funny. But Pepper was putting on a show when she was with him.

Tony was- Tony was just- Tony was everything Pepper had ever wanted. He's gorgeous, funny, sweet, charming. He was her friend and her confident. Pepper didn't need to be another person around him because after eight years of working for him, they knew each other. Inside and out. But he was her _boss_. A figure of authority. And they had both avoided the tension for so long, Pepper didn't know if starting something would even be worth the hassle.

/

Business trips weren't always so bad. Except for when they stopped Pepper being whisked off to somewhere romantic with her current boyfriend, Jake.

It was a 'necessary' weekend of conferences and meetings and scheduling. Tony had a TV appearance on three morning breakfast shows and two evening shows. To add to it the whole board were flying out to supervise the weekend too, which only put more pressure on Pepper's organisation skills.

The meetings were long. Dull, boring and if anything completely _unnecessary_. Pepper sat through them day dreaming about anything and everything. She was as bad as Tony and had taken to doodling random pictures of whatever popped into her brain. She laughed lightly to herself thinking how she was so alike Tony. However she hastily _stopped_ thinking that because those thoughts could only lead to more feelings.

The conferences were also a load of pointless nonsense. Army generals and machinery specialists giving lectures to reporters who didn't really care and were only there because they heard Tony Stark would make an appearance. What they didn't seem to notice thought was that was _all_ Tony was going to do. He stood to the side with Pepper and every now and then cracked some joke about who was talking. That got Pepper through the conferences.

And the TV appearances went surprisingly well. The board were sceptical that Tony would say something stupid and cause everyone a weight load of work, but he was well behaved. He was on time for the morning shows and answered the questions without giving too much away. And the evening shows he was just as well mannered. He was so good in fact that the board suggested a night out on the town as a 'congrats' present to Tony.

And that was where the confusion began more.

They had all gone out for a meal first. It was a quiet, chatty, pleasant evening which couldn't have run more smoothly. Everyone was getting along and as they had the next day off, everyone decided to go to a bar afterwards. Pepper was the only woman and was being constantly hit on by drunken board members. Pepper grimaced, but was thankful for Tony as he managed to fend them off in a non suggestive way. People started dropping like flies and disappearing one by one, until eventually it was just Pepper and Tony left out of the Stark Industries clan.

They were sitting in a booth and both hadn't noticed their party had slowly dissipated. Tony eventually turned to ask who wanted more drinks and realised that he didn't know anyone else in the bar. It was now full of big, rowdy groups and love sick couples. Tony ordered two drinks from a passing waitress before turning back to Pepper.

"Did you notice everyone leaving?"

Pepper scanned the room slowly before raising her eyebrows and looking back at Tony. "When did they go?" They both had smiles on the faces and Pepper let a burst of laughter out. "Alright, seems like it's just us then."

"Seems so." Tony answered with a sparkle in his eye and a smile gracing his mouth.

Pepper caught sight of that smile. _That_ smile. Pepper knows that smile was just for her. She felt big headed whenever she ran it through her mind, but it's true. Tony flirted with her _a_ _lot_. And Pepper had started to feel his genuine interest in _her_ over the past few months. And that smile- _that_ smile just did things to her. Her stomach dropped when she looked at Tony across the booth and a tingle ran through her body.

Pepper cleared her throat before yawning for affect, "I better get to bed, we have an early flight."

"I just ordered us drinks though Pepper," Tony crossed his arm to her and watched her intently.

Pepper was half way edging out of the booth, her legs were swung over the side. Tony's hand on top of hers stopped her. She looked back at him and debated how much harm one more drink could do. And she thought it could do a _lot_. So Pepper pulled her hand from under Tony's and stood. "I'm tired. I'd rather just go to bed. Sorry."

Tony stood abruptly, "It's alright, and I'm pretty drained myself anyway. I'll walk up with you."

They both turned to leave.

Tony and Pepper were standing side by side in the elevator. Tony had his hands tucked away in his pockets and Pepper was fiddling with her shoes as she had taken them off because they were hurting her feet. Pepper didn't feel quite as relaxed, probably because she knew they were both buzzed from drinks and both clearly had a thing for each other.

"So," Pepper's voice croaked out. "The car will pick us up at nine. And the flight should hopefully be leaving at ten."

Tony nodded.

"Shall I wake you up?"

Tony looked in Pepper's direction and shook his head. "It's alright, i'll just get a wakeup call."

Pepper nodded and focused her eyes on the elevator doors. She squeezed them shut and prayed that they would arrive at her floor already. She didn't want to be in such an enclosed space with Tony for much longer. Her prayers were answered when a 'ding' rang through the air signalling that they were at a floor.

She opened her eyes and saw that they were on floor seven. Her floor. She turned to Tony and saw that he was watching her.

"What?"

"Just wondered what you were doing with your eyes closed," he answered with a hint of a smile.

Pepper momentarily panicked she had been caught out. But she composed herself quickly and started to back out of the doorway. "So tomorrow morning yeah?"

"Yeah."

They both stood awkwardly looking at each other. Tony took initiative and leaned in for a hug. He wrapped his arms around her waist and securely held on to her. Pepper returned the hug by enveloping her arms round Tony's neck and burying her face into his shoulder. They both enjoyed the proximity for a few seconds before Pepper remembered Jake and pulled back.

"Okay, i'll be off now."

Tony nodded again. He leant in again, but this time to kiss Pepper's cheek. He put one hand on her forearm and leaned so that he didn't get too close or too excited. The fact she was with Jake hurt Tony bad, but he didn't like making it awkward for her so tried to be strong around her. But when Pepper gave in too, Tony had no chance.

As Tony started pulling back, Pepper's arm involuntarily wrapped around Tony's jacket lapel. This obviously stopped Tony and his eyes flew from her hand to her eyes. He wasn't sure what was going on, she was staring at him and looked in deep thought. After a split second of heavy breathing Pepper threw herself at Tony. Her lips landing right on his.

Tony was pushed back by the force of Pepper and his back slammed into the back of the elevator. Tony rocked back with his arms on Pepper's hips so that she didn't go too far out. The doors started to close again, but Tony stuck one arm out so that they didn't crush him and Pepper.

Pepper could feel them both easing into the kiss now. Her hands were wrapped around his neck and she felt one of Tony's hands gripping at her hip. The other hand she assumed was stopping the doors from closing again. She was feeling all kinds of things she hadn't felt with Jake after _months_. And this was only hers and Tony's _first_ kiss. Her stomach was doing summersaults and butterflies were fluttering in the pit. A shiver ran down her spine as she felt Tony digging his fingernails into her skin showing his want.

After a few breathless minutes of locking lips, Pepper pulled away. Leaving an aroused and ecstatic Tony Stark hanging in the frame of the elevator. Pepper leaned against the back wall as her knees felt weak, and she ran her thumb at her lips, perfecting her lipstick once again. All before bidding Tony good night and walking down the hall way to her room.

As Pepper closed her hotel room door and leant against it, the realisation of what had just happened between her and her boss. She had kissed him for a good few minutes and surprisingly, she didn't regret it. Pepper wanted to do it again if anything. She would have thought she would be mortified and want to quit. But it was so different for her to kiss someone who she had a relationship with already. Her and Tony may not have been dating per say, but they may as well have really. They had never just made the move.

Her thoughts were broken by a knock at the door. _Tony_. Pepper jumped from it and studied the door handle, _should she open it_? She _was_ just thinking about how much she wanted to do it again. Another hard knock came and Pepper went to open it.

"Hey."

_Jake._

"Pepper?"

_Jake. Why him?_

"Hello, Pepper?"

Pepper composed herself and put on a fake smile, "Hey Jake. What you doing here?"

Pepper turned to an angle to let Jake in. He dragged his back in and had a champagne bottle in his hand. He smiled smugly and all Pepper wanted to do was go back to the elevator, press button number nine, bang on Tony's door and then do the same thing to Tony. "I just thought we could have a nice night here as I couldn't take you away."

Pepper smiled back. Another fake smile. "I just wished you had called ahead, I feel a bit unprepared." Pepper laughed nervously. She really wasn't in the mood and could tell Jake had just come up because his plans for a weekend of sex had been ruined. Her mind was racing with images of her and Tony and she didn't feel like spending the night with Jake.

Jake made an awkward face, "Sorry to surprise you. I just thought it'd be a romantic gesture. I'm just going to go freshen up, then we can have champagne and enjoy the night." He grinned before walking round the corner and into the bathroom. Pepper breathed out and tried to ready herself for a long night.

Another knock at the door broke her thoughts.

She whipped round. _Tony._

Pepper tiptoed towards the door, as to not let Jake hear. She turned the handle and lo and behold, there was a shiny eyed, ragged and gorgeous looking Tony Stark.

"Pepper I-" Tony abruptly stopped talking when Pepper shoved his chest back and stepped out into the hotel hallway with him. "What's the matter?"

Pepper watched him and bit her lower lip. "Jake turned up. He said he wanted to spend a 'romantic' evening with me as work got in the way of our mini holiday. He's in the bathroom now." Pepper felt guilty, but she couldn't fully understand why she felt like she was cheating on Tony rather than on Jake.

"Oh," Tony's eyes shone with brimming tears, he took a hard swallow. "Mr. Romantic screwing things up again." He laughed awkwardly.

Pepper stepped towards Tony. But only he countered her movement and stepped away. "Tony-"

"No hey," Tony cut her off. "He's your boyfriend right Potts." He looked down the hallway and then down at his feet. Anything but in Pepper's eyes because he knew he might go crazy if he looked at her and knew she was about to spend the night with another man. "I guess i'll just, you know."

He briskly turned with the full attention of drinking himself into oblivion. Pepper grabbed his hand before he could get too far though. "Tony. He surprised me. I thought it was going to be you knocking at the door."

Tony was trying to not lose control, "Looks like I was five minutes too late huh?"

"Tony," Pepper looked at their joint hands, then back into his eyes. She felt an overwhelming wave of courage. And her feelings for Tony were just slowly becoming too much for her to handle. She wanted _him_ tonight. "Shall I tell Jake to go?"

Tony considered it. _Really_ considered it. He had wanted Pepper for a long time and she was offering it to him. She was offering everything he had ever truly wanted. But she was happy with this other guy. If Tony wasn't in the picture she could and _would_ be happy with Jake. Tony didn't want to be selfish. As much as he _did_ want Pepper.

"No." He shook his head, "Jake's a good guy."

"So are you." Pepper answered almost desperately.

Tony reached out to stroke Pepper's cheek gently. "I know."

And with that Tony turned down the hallway.

**I may do more. I may not. You decide? AnnaTW :)**


	2. Chapter 2

**Wow, sorry, I forgot about this story. Then re-read it and felt **_**so**_** bad for it being so stupidly late. Thank you for the reviews as well you lovelies! :)**

Pepper didn't know what to say. She watched Tony walk away down that hallway and just didn't know what to do. That night had been magical. Her and Tony talking for hours, not even noticing everyone else leaving. And then that kiss. _The_ kiss which made Pepper forget all about professionalism, that made her consider dumping Jake, that made Pepper want Tony out of anyone else.

After she saw Tony turn the corner of the hallway towards his own room, or the bar to drink himself silly, Pepper wasn't sure where he'd go, she went back into the room with Jake. He was there with champagne and a clean shirt on. Once Pepper closed the door and made an excuse about room service getting the wrong door. She gritted her teeth and intended on getting through the night, but Tony's face kept flashing in her mind and she just couldn't do it. After downing the glass of ice cold champagne Jake handed her, Pepper told him she couldn't be with him anymore.

Understandably, Jake was confused and then got a bit angry because Pepper's change of mind was so out of the blue. It took her some time to calm him down and explain how she just didn't feel their relationship going anywhere. It also took her some time to get him out of her room, it seemed as though Jake was expecting some break up sex. After a while Pepper just straight out told him to go and was left all alone in her large hotel suite.

All alone and thinking about Tony. She had no other way of taking her mind off of it. TV was dull, no one was answering their phones and no matter how many times she rolled over she just could not get to sleep. All because she knew where Tony was. He was in room three hundred and eighty four on floor six, only one floor down. And he was on his own.

And she was on her own. Lonely, vulnerable and _single_.

But Pepper wasn't a hundred percent sure she could do that. She was never one to be spontaneous, especially when it came to her love life. She didn't like to make a fool of herself. Tony was such a huge part of her life as well, and she didn't even fully know what she felt about the situation yet. She didn't want to embarrass herself and make the situation any worse by going down to see him, giving him false hope and then running away. But Pepper couldn't see herself running away. Where would she run? Who would she run to? The only person she could even consider herself running to would be Tony.

So why wouldn't she go down to see Tony.

/

Tony did go to his room. He wasn't going to go to a bar and get hammered just so it would be less painful to hook up with a random girl. All out of bitterness that Pepper was with Jake and not him. Tony didn't want that. He wanted Pepper, so there would be no reason for him to do it. The first thing he had done when he got to his room was strip his clothes. He's dark, silky, expensive suit lay on the floor in a heap. He threw on a pair of black shorts and a white t-shirt before slumping on the sofa in front of the TV. He tried to distract himself.

However Tony didn't realise that the best distraction was currently standing outside his doorway, fidgeting her feet and biting on her lip. Pepper kept bringing a hand up to knock on the door before pulling it down to her side again. Then rehearsing what she was going to say, but was never happy with it and so tried to think of something else. In that moment all Pepper wanted to do was kiss Tony again.

So she knocked.

Tony whipped his eyes from the TV to stare and furrow his eyebrows at the door. He didn't remember ordering room service. He pushed himself off of the sofa and walked to the door. He opened the door in preparation to tell them they had the wrong room before he saw Pepper and bit his tongue immediately.

"Pepper."

"Tony."

"What-" Tony furrowed his eyebrows again, "I thought you were with Jake tonight?"

Pepper fidgeted again, "Yeah I was. But I sent him home."

Tony looked up and down the empty hotel doorway. He sighed and looked at back at the woman in front of him. "Pepper you shouldn't have done that."

Pepper took a step back, "What?"

"Jake was-" Tony scratched the back of his neck. "Jake was a nice guy. Why did you send him away? I thought you were happy dating him."

"I was happy Tony," Pepper countered her movement and stepped towards Tony again. "But it changed tonight." Her eyes searched his. "We spent hours just talking. Just us. And it was better than any date I'd had with Jake before." Pepper took another step forward, into Tony's personal space. "And then that kiss."

"That kiss was like a wakeup call Tony." Tony's breath caught in his throat as he looked down at Pepper standing mere inches from him. Her hand brushing his lightly as it hung by her side. "And the second I saw you outside my door I knew you had felt it too."

Pepper took the courage to raise her hand to Tony's chest. She slid it up and around his shoulder until she was cupping his cheek. She felt Tony's hands reach to hold her waist. "And in that moment I realised."

"Realised what?" Tony breathed out, Pepper was leaning closer.

"That Jake was the last person I wanted."

Pepper closed the tiny gap left and pressed her lips to Tony's. His arms circled round her waist and his fingers gripped the material of her clothes. Pepper rose to her tiptoes so that she could kiss him easier. Her own hands wound into his hair and scratched at his neck. And they both felt better. Kissing in the doorway of Tony's hotel suite.

**Another chapter, well over due. SOSOSO sorry again. Life has been hectic. I love you all :3**


	3. Chapter 3

**Thank-you for the reviews lovelies!**

They kissed for a good few minutes in the hallway. Slowing the pace every now and then to savour the moment they didn't get to make the most of in the elevator. The next they sped the kiss and explored each other's bodies as much as they could. It felt weird for both of them to be able to do this without any consequences anymore. It didn't even register that they were still in the hotel hallway until a maid made her presence knowing by clearing her throat. Pepper turned bright red and buried her face in Tony's chest, whilst he pulled her closer to him so that the maid and her trolley could get past. He could feel Pepper laughing against his neck and he smiled at the sincerity of the moment.

Once the maid had gone and turned the corner Pepper peeled herself from Tony's body and smiled up at him. Tony's smile shone back at her. "So you didn't want Jake huh?"

"Nope. I wanted a hero." Pepper bit her lip and grinned. "A superhero to be exact."

Tony linked his hands at the base of her back and looked thoughtful. "You know it's funny you say that, because I happen to be the best superhero around."

"Oh really?" Pepper countered Tony's movement and linked her hands at the nape of his neck. she fiddled with the small hairs there. "Well i'm glad I came to your door then. Because I distinctly remember Tom Harding trying to convince me he was a better Iron Man than you at the bar earlier. And he's only four doors down."

"As in the head of marketing Tom Harding?" Pepper nodded, "Please don't make me laugh. He couldn't tell a screwdriver from a spanner."

"Do I detect a hint of jealousy Mr. Stark?" Pepper angled her head towards Tony. She was finding it almost endearing how Tony was acting. He hadn't let go of her still.

"I could never be jealous of Tom Harding," Tony leant down closer to her lips again. "Unless he's talking to you when i'm not of course."

Just as Tony's lips were about to touch hers again, Pepper opened her mouth. "As much as i'm loving this. Right here," her hands slid down his chest and rested at the waistband of his shorts. "Right now. Shouldn't we really consider continuing this _inside_ the hotel room? Unless you want another maid to come along and interrupt us again."

Tony grinned and pecked her lips before stepping back and giving Pepper room to walk in ahead of him. "After you."

/

They didn't have sex that night. Not saying they didn't do other things, but they both just felt content enough to be allowed to be kissing and touching and spending _unprofessional_ time together. They talked and joked and discussed the possibility of a relationship. But they both eventually fell asleep on the bed, Pepper in her underwear and Tony in his shorts.

When Pepper woke up she tried to tiptoe around the room to not wake Tony whilst she put on her dress from the night before and tried to smarten herself out. She would have much rather stayed cuddled up to Tony, but their flight was soon and Pepper was in the wrong room. Tony did wake up briefly and mumbled to her from his position on the bed, face down on the bed and asked what she was doing. Pepper started to nag him telling him he had to meet her in the lobby in forty five minutes and left for her own room. But not before rolling him over and giving him a long, slow kiss. Just to remind him of what happened between them the night before.

An hour later, Tony made his way to the lobby in his jeans and polo shirt. He couldn't stop grinning at the way the night had turned out in his favour. They had practically had a date ending with a mind blowing kiss, then resulting in Pepper spending the night with him. Although for a short while Tony did think he had lost Pepper to Jake, things looked up eventually. He didn't have to wait for Pepper long, she turned up eventually in a slimming dress and waved him over to the front desk.

Tony jogged over and smiled sweetly, "Hey."

"Morning Tony," Pepper grinned back at him. "I need the company card to check out."

"Oh sure," Tony put down his bag and dug in his back pocket for his wallet. He got out the card and turned to the receptionist to check out himself. "Hi, can I check out the Stark Industries party please and cover any costs."

"Of course." The receptionist smiled. He took the card off of Tony and began clicking away on his computer. Thankfully he obviously wasn't fazed by Tony's status as it was a high class hotel and so he probably ran into celebrities all the time.

Pepper took Tony's attention away by nudging him in the arm. "You okay?"

Tony smiled at Pepper. She clearly wanted some attention from Tony. He put his hand on her waist to keep her a bit closer. "I'm great thank you. You okay?"

Pepper beamed back, "Fantastic."

"If you could enter your pin please Mr. Stark." The receptionist interrupted the moment. Tony did so and took his card back. "Right there you go sir. I hope you both had a pleasant stay, have a good day."

"I'm sure I will. You too buddy." And with that Tony and Pepper turned to walk off. Intending to go back to Tony's beach side house and relax. Their plans were momentarily stopped as they saw Jake Henderson exiting the elevator. He's eyes moved to Tony and Pepper hand in hand. "Oh great."

Tony looked at his side to see Pepper's cheeks growing a darker shade of pink. Jake looked at their hands then back up at their faces. He rolled his eyes and headed towards the reception himself. Pepper stepped away from Tony and explained how she wanted to talk to Jake quickly. Tony understood, but reluctantly let go of her hand.

"Jake," Pepper rushed over to him and stopped him by putting her hand on his shoulder. "Jake, please don't be angry. You and I both know we went going anywhere." Pepper smiled sympathetically, trying to justify her actions.

"I'd flown out to see you Pepper. I really like you." Jake shook his head, "I really _liked_ you."

Pepper looked at her feet and fidgeted. That sure made her feel like crap. "I'm really sorry. I just thought that there wasn't any harm in ending it now rather than later so that we haven't wasted all that time."

Jake nodded, "Well i'm glad you stopped me from wasting my time." He forced a swallow, "I thought we could have gone somewhere, but clearly I was mistaken." Jake looked Pepper in the eye for a long moment before walking in the opposite direction.

Pepper looked down at her feet. She felt awful. Jake obviously really liked her and thought that they maybe actually amount to something. However relationships are a two way thing and Pepper couldn't beat herself up about not giving Jake false hope. That's what Pepper told herself anyway. Especially as she turned around and saw Tony looking almost sombre all on his own. He was her best friend.

"Sorry about that," Pepper strolled back over to Tony and tried to act nonchalant. The feeling of guilt about Jake would ware off eventually she hoped. "Just needed some closure."

Tony studied her for a moment, "Are you okay?"

"I'm fine," Pepper took his hand in hers and linked their fingers. So perfect. "Let's go home."

**Proud of myself that this update didn't take a million months. Love to all!**


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